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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This sub-file is made of two letters between O.O. Alwyne Westmoreland ('32) and the Headmaster, John Buchannan, regarding the forthcoming Development Campaign.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This sub-file focusses on two letters bet the Headmaster, John Buchanan, and O.O. Alwyne John Westmoreland ('32) regarding Oakham School winning the Ashburton Shield in 1966.

A letter from the Headmaster Nigel Lashbrook to Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

This sub-file is made of two letters from Roger Blackmore regarding OSEL accounts for the year 1984-1985.